Triethylamine → HCID 59764775, Verbindung

HRID 406465

Reaktionsgleichung

Reaktionsgleichung von HRID 406465
Cl.Cl.[C:3]1([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[N:27]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=1)=[C:28]=[O:29]>ClCCl>[CH3:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][NH:27][C:28]([N:17]2[CH2:18][CH2:19][CH:15]([N:12]3[CH2:11][CH2:10][CH:9]([C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH2:14][CH2:13]3)[CH2:16]2)=[O:29])=[CH:32][CH:33]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27333881-(Isocyanatomethyl)-4-methylbenzeneHCID 68899888HCID 68899888, Verbindung

Produkt 1

HCID 59764775HCID 59764775, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride (preparation #7) (0.050 g, 0.165 mmol) and triethylamine (0.092 mL, 0.66 mmol) in dichloromethane (1 mL) was added 1-isocyanatomethyl-4-methyl-benzene (0.024 g, 0.165 mmol) and the reaction mixture was stirred at ambient temperature for about 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel using 5% MeOH/EtOAc as the mobile phase to give 3-(4-phenyl-piperidin-1-yl)-pyrrolidine-1-carboxylic acid 4-methyl-benzylamide (0.042 g, 68%). RP-HPLC (Table 1, Method b) Rt 1.72 min; m/z: (M+H)+ 378.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography on silica gel using 5% MeOH/EtOAc as the mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-28fcf59ea7be42fda0561fec2ceba150
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754107B2

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